Windstar

Wind Star: Upcoming Sailings

Windstar's Wind Star sailing yacht sailing at sunset.

Upcoming Windstar Cruises Aboard the Wind Star

27 Results

Taxes and fees included in all prices shown

Sort

A beautiful daytime view of the iconic windmills of Mykonos, Greece, with their white-washed walls and thatched roofs against a vivid blue sky.

Windstar

7-night Treasures Of The Greek Isles Cruise From Piraeus (Athens), Greece

Athens (Piraeus)

Kusadasi (Ephesus)

Aboard

Wind Star

From

Piraeus (Athens), Greece

18 Sailings

Jun 13 - Oct 10, 2026

18 Sailings

Jun 13 - Oct 10, 2026

Published prices from

$2,417

per person*

taxes & fees included

A beautiful daytime view of the iconic windmills of Mykonos, Greece, with their white-washed walls and thatched roofs against a vivid blue sky.

Windstar

10-night Delphi and Meteora: Grecian Treasures Cruise/Land Package From Piraeus (Athens), Greece

Athens (Piraeus)

Kusadasi (Ephesus)

Aboard

Wind Star

From

Piraeus (Athens), Greece

17 Sailings

Jun 17 - Oct 7, 2026

17 Sailings

Jun 17 - Oct 7, 2026

Published prices from

$6,872

per person*

taxes & fees included

Microlimano harbor in Piraeus, Greece at sunset.

Windstar

10-night Enchanting Meteora, Greece, And Amalfi Coast Cruise/Land Package From Piraeus (Athens), Greece

Athens (Piraeus)

Aboard

Wind Star

From

Piraeus (Athens), Greece

1 Sailing

Oct 14, 2026

1 Sailing

Oct 14, 2026

Published prices from

$5,617

per person*

taxes & fees included

A beautiful wide shot of the Port of Portoferraio on Elba Island, Italy, showcasing the historic town's terracotta-roofed buildings and fortifications sprawling up the hillside from the blue sea.

Windstar

14-night Star Collector: Ancient To Avant-Garde Mediterranean Cruise From Piraeus (Athens), Greece

Athens (Piraeus)

Strait of Messina

Aboard

Wind Star

From

Piraeus (Athens), Greece

1 Sailing

Oct 17, 2026

1 Sailing

Oct 17, 2026

Published prices from

$7,436

per person*

taxes & fees included

A beautiful hillside view of the colorful, clifftop houses of Sorrento, Italy, overlooking the brilliant blue Tyrrhenian Sea on a sunny day.

Windstar

7-night Enchanting Greece & The Amalfi Coast Cruise From Piraeus (Athens), Greece

Athens (Piraeus)

Strait of Messina

Aboard

Wind Star

From

Piraeus (Athens), Greece

1 Sailing

Oct 17, 2026

1 Sailing

Oct 17, 2026

Published prices from

$3,917

per person*

taxes & fees included

A panoramic sunset shot of the beautiful harbor in Palma de Mallorca, Spain, with a marina full of boats and buildings on the surrounding hills.

Windstar

17-night Star Collector: Romance Of The West Med Cruise From Civitavecchia, Rome, Italy

Rome (Civitavecchia)

Aboard

Wind Star

From

Civitavecchia, Rome, Italy

1 Sailing

Oct 24, 2026

1 Sailing

Oct 24, 2026

Published prices from

$7,578

per person*

taxes & fees included

St. Peter's Basilica, Rome cityscape at sunset.

Windstar

7-night Mediterranean Island Mosaic Cruise From Civitavecchia, Rome, Italy

Rome (Civitavecchia)

Aboard

Wind Star

From

Civitavecchia, Rome, Italy

1 Sailing

Oct 24, 2026

1 Sailing

Oct 24, 2026

Published prices from

$3,954

per person*

taxes & fees included

Plaza Mayor in Madrid, Spain.

Windstar

14-night Next Stop Madrid: Spanish Treasures Cruise/Land Package From Madrid, Spain

Barcelona (Tarragona)

Palma de Mallorca

Aboard

Wind Star

From

Madrid, Spain

1 Sailing

Oct 27, 2026

1 Sailing

Oct 27, 2026

Published prices from

$8,715

per person*

taxes & fees included

Belém Tower on Tagus River.

Windstar

24-night Star Collector: Classic Crossing To Spain & More Cruise From Barcelona, Spain

Barcelona (Tarragona)

Palma de Mallorca

Cartagena (Spain)

Aboard

Wind Star

From

Barcelona, Spain

1 Sailing

Oct 31, 2026

1 Sailing

Oct 31, 2026

Alcazaba fortress in Malaga.

Windstar

10-night Treasures Of Southern Spain & Morocco Cruise From Barcelona, Spain

Barcelona (Tarragona)

Palma de Mallorca

Cartagena (Spain)

Aboard

Wind Star

From

Barcelona, Spain

1 Sailing

Oct 31, 2026

1 Sailing

Oct 31, 2026

Published prices from

$4,415

per person*

taxes & fees included

Rocky beach and palm trees in Barbados.

Windstar

14-night Ocean Crossings Cruise From Lisbon, Portugal

Bridgetown (Barbados)

Aboard

Wind Star

From

Lisbon, Portugal

1 Sailing

Nov 10, 2026

1 Sailing

Nov 10, 2026

Published prices from

$4,786

per person*

taxes & fees included

An aerial view of the colorful waterfront of St. George's, Grenada, with the town's buildings nestled on a hillside and a long, rocky breakwater extending into the calm, turquoise water.

Windstar

25-night Star Collector: Southern Caribbean Thanksgiving Jubilee Cruise From Lisbon, Portugal

Bridgetown (Barbados)

Aboard

Wind Star

From

Lisbon, Portugal

1 Sailing

Nov 10, 2026

1 Sailing

Nov 10, 2026

Rocky beach and palm trees in Barbados.

Windstar

18-night Star Collector: Reefs & Rainforests: The Caribbean, Colombia, Panama & Costa Rica Via The Panama Canal Cruise From Bridgetown, Barbados

Bridgetown (Barbados)

Aboard

Wind Star

From

Bridgetown, Barbados

1 Sailing

Nov 24, 2026

1 Sailing

Nov 24, 2026

Colorful colonial balconies in Cartagena.

Windstar

11-night Colombian & Southern Caribbean Coastlines Cruise From Bridgetown, Barbados

Bridgetown (Barbados)

Aboard

Wind Star

From

Bridgetown, Barbados

1 Sailing

Nov 24, 2026

1 Sailing

Nov 24, 2026

Published prices from

$6,851

per person*

taxes & fees included

National Theatre of Costa Rica in San José.

Windstar

10-night Monteverde Cloud Forest & Arenal Volcano Cruise/Land Package From Colon, Panama

Golfo Dulce (Puerto Jimenez)

Aboard

Wind Star

From

Colon, Panama

3 Sailings

Dec 5, 2026 - Jan 2, 2027

3 Sailings

Dec 5, 2026 - Jan 2, 2027

Published prices from

$5,255

per person*

taxes & fees included

An aerial view of the bustling city of Balboa, Panama, with a scenic coastal road alongside a marina and tall modern skyscrapers in the background.

Windstar

7-night Costa Rica & Panama Canal Cruise From Colon, Panama

Golfo Dulce (Puerto Jimenez)

Aboard

Wind Star

From

Colon, Panama

3 Sailings

Dec 5, 2026 - Jan 2, 2027

3 Sailings

Dec 5, 2026 - Jan 2, 2027

Published prices from

$2,855

per person*

taxes & fees included

National Theatre of Costa Rica in San José.

Windstar

11-night Monteverde Cloud Forest & Arenal Volcano Cruise/Land Package From San Jose, Costa Rica

San Jose (C.R.)

Puerto Caldera (Puntarenas)

Aboard

Wind Star

From

San Jose, Costa Rica

2 Sailings

Dec 8 - Dec 22, 2026

2 Sailings

Dec 8 - Dec 22, 2026

Published prices from

$5,465

per person*

taxes & fees included

A cruise ship navigating through the Gatun Locks of the Panama Canal, an important navigational route and popular tourist destination.

Windstar

7-night Costa Rica & Panama Canal Cruise From Puerto Caldera, Costa Rica

Puerto Caldera (Puntarenas)

Golfo Dulce (Puerto Jimenez)

Aboard

Wind Star

From

Puerto Caldera, Costa Rica

3 Sailings

Dec 12, 2026 - Jan 24, 2027

3 Sailings

Dec 12, 2026 - Jan 24, 2027

Published prices from

$3,065

per person*

taxes & fees included

A close-up shot of two cougars, or pumas, resting on a rocky ledge. The cougar in the foreground looks directly at the camera, its tawny-colored face and alert eyes focused, while the other cougar is curled up and resting behind it.

Windstar

29-night Star Collector: Panama Canal Ocean Crossing To Tahitian Dreams Cruise From Colon, Panama

Golfo Dulce (Puerto Jimenez)

Aboard

Wind Star

From

Colon, Panama

1 Sailing

Jan 31, 2027

1 Sailing

Jan 31, 2027

Published prices from

$8,321

per person*

taxes & fees included

A cruise ship navigating through the Gatun Locks of the Panama Canal, an important navigational route and popular tourist destination.

Windstar

8-night Costa Rica & Panama Canal Cruise From Colon, Panama

Golfo Dulce (Puerto Jimenez)

Aboard

Wind Star

From

Colon, Panama

1 Sailing

Jan 31, 2027

1 Sailing

Jan 31, 2027

Published prices from

$5,570

per person*

taxes & fees included

A picturesque view of a brick lighthouse perched on the lush, green cliffs of Maroe Bay, Huahine, with the ocean and a blue sky in the background.

Windstar

36-night Star Collector: Pacific Horizons From Panama To Tahiti Cruise From Colon, Panama

Golfo Dulce (Puerto Jimenez)

Aboard

Wind Star

From

Colon, Panama

1 Sailing

Jan 31, 2027

1 Sailing

Jan 31, 2027

Lush rainforest and beach in Costa Rica.

Windstar

28-night Star Collector: Passage To French Polynesia Cruise From Puerto Caldera, Costa Rica

Puerto Caldera (Puntarenas)

Aboard

Wind Star

From

Puerto Caldera, Costa Rica

1 Sailing

Feb 8, 2027

1 Sailing

Feb 8, 2027

Lush rainforest and beach in Costa Rica.

Windstar

21-night Ocean Crossings Cruise From Puerto Caldera, Costa Rica

Puerto Caldera (Puntarenas)

Aboard

Wind Star

From

Puerto Caldera, Costa Rica

1 Sailing

Feb 8, 2027

1 Sailing

Feb 8, 2027

Published prices from

$5,035

per person*

taxes & fees included

A scenic view of Moorea, French Polynesia, with turquoise lagoons, a row of luxurious overwater bungalows, lush palm trees along the coast, and a distant island under a stunning blue sky.

Windstar

10-night Moorea Magic Overwater Villa Cruise/Land Package From Papeete, Tahiti, French Polynesia

Aboard

Wind Star

From

Papeete, Tahiti, French Polynesia

42 Sailings

Feb 26 - Dec 24, 2027

42 Sailings

Feb 26 - Dec 24, 2027

Published prices from

$4,818

per person*

taxes & fees included

A scenic view of Moorea, French Polynesia, with turquoise lagoons, a row of luxurious overwater bungalows, lush palm trees along the coast, and a distant island under a stunning blue sky.

Windstar

10-night Bora Bora & Beyond Cruise/Land Package From Papeete, Tahiti, French Polynesia

Aboard

Wind Star

From

Papeete, Tahiti, French Polynesia

42 Sailings

Feb 26 - Dec 24, 2027

42 Sailings

Feb 26 - Dec 24, 2027

*Rates and offers are per person, in US Dollars, based on double occupancy, capacity controlled, subject to availability and confirmation, and may change without notice. Government taxes and fees are included. Rates and offers are available for select dates and categories only. Additional restrictions may apply. Call 1-800-377-9383 for full terms and conditions.